Water → [1-(4-Acetyl-phenyl)-piperidin-4-yl]-acetic acid ethyl ester

HRID 2262705노트

반응식

HRID 2262705 반응식
Cl.[CH2:2]([O:4][C:5](=[O:13])[CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH3:3].F[C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH2:2]([O:4][C:5](=[O:13])[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][CH:16]=2)[CH2:9][CH2:8]1)[CH3:3]

참가 물질

6

반응물 4

HCID 962WaterHCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 45358839Piperidin-4-yl-acetic acid ethyl ester hydrochloride

생성물 1

HCID 57442326[1-(4-Acetyl-phenyl)-piperidin-4-yl]-acetic acid ethyl ester

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
90 °C

실험 절차

To a solution of piperidin-4-yl-acetic acid ethyl ester hydrochloride (24 mmol) in anhydrous DMSO (20 mL) is added 1-(4-fluoro-phenyl)-ethanone (24 mmol) and potassium carbonate (24 mmol). The resulting mixture is heated at 90° C. for 36 hr. The reaction mixture is allowed to cool to rt, poured into cold water (100 mL), and extracted with EtOAc (40 mL×3). The combined organic layers are washed with water and brine, dried over sodium sulfate, and concentrated. The crude product is purified through silica gel flash chromatography (hexane/ethyl acetate 2:1) to give the title compound as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.86 (2H, d), 6.85 (2H, d), 4.15 (2H, q), 3.89 (2H, br, d), 2.90 (2H, dt), 2.51 (3H, s), 2.27 (2H, d), 2.04 (1H, m), 1.83 (2H, br, d), 1.38 (2H, dt), 1.27 (3H, t); LC-MS (M+1): 290.

후처리

  1. temperatureto cool to rt
  2. extractionextracted with EtOAc (40 mL×3)
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product is purified through silica gel flash chromatography (hexane/ethyl acetate 2:1)

출처 및 근거

ORD 기록
ord-3148f61b56fa469eae329d04404b48eb
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851474B2

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